Hydrochloric Acid → HCID 178496278, compound

HRID 1407108Notes

Reaction equation

[N:1]([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1[NH2:8].Cl.[CH3:15][O:16][CH2:17][C:18](=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21].CC([O-])=O.[Na+]>O.CO>[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1[NH:8][N:1]=[C:19]([C:18](=[O:24])[CH2:17][O:16][CH3:15])[C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of NaNO2 (1.66 g, 24 mmol) in H2O (5 mL) was added dropwise at 0° C. to a mixture of 2-fluoro-4-iodoaniline (4.74 g, 20 mmol) and 6 M HCl aqueous solution (20 mL, 120 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (2.59 mL, 20 mmol) and NaOAc (9.84 g, 120 mmol) in MeOH (40 mL) pre-cooled at 0° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with saturated NaHCO3 aqueous solution and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from hexane/AcOEt to give the title compound (6.29 g, 80% yield) as yellow crystals: mp 141-146° C.; 1H NMR (300 MHz, CDCl3): δ ppm 3.50 (3H, s), 3.93 (3H, s), 4.64 (2H, s), 7.35 (1H, t, J=8.5 Hz), 7.49-7.55 (2H, m), 12.97 (1H, br s).

Workup

extractionextracted with AcOEt
washThe extract was washed with saturated NaHCO3 aqueous solution and brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from hexane/AcOEt

Sources & evidence

ORD record: ord-ab7f3574a05b4fd4bff3df9e874586c2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916566B2

Reaction notes

Loading…